Benzyl Bromide → Tert-butyl 3-(benzyloxy)azetidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-butyl 3-hydroxyazetidine-1-carboxylate (21) (1 gm, 5.77 mmol) was dissolved in dry DMF (15 ml) and was cooled to 0° C. under nitrogen and was added sodium hydride (0.35 gm, 8.66 mmol). The reaction mixture was allowed to stir at room temperature for 30 min and was added benzylbromide (22; 1.08 gm, 6.35 mmol) at 0° C. The reaction mixture was then allowed warm to room temperature and stirred for 2 h. After completion of the reaction it was quenched by the addition of sat. ammonium chloride solution and extracted with ether. The organic layer was then dried over sodium sulfate and concentrated under vacuum. The crude product was purified column chromatography to yield compound 23 (1.21 gm, 80%).

Provenance & Evidence